Middleburg Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Your Middleburg Vacation

With every last detail planned before you go away, our Middleburg vacation packages mean you can focus more on letting the good times roll. Whether you stay in the neighborhood of Stone Ridge, which is good for walking, or someplace else in town, this lively city promises a world of discoveries. You'll want to take in the sights during your trip to Middleburg. Carve out some time for major attractions such as Greenhill Winery & Vineyards, Cana Vineyards and Winery and Chrysalis Vineyards. A few quick clicks is all it takes to put together the ultimate Middleburg vacation on Expedia.

Ready to book your vacation to Middleburg?

 

Choose your dates

Middleburg Hotel Deals

Salamander Resort And Spa

Salamander Resort And Spa

5 out of 5
500 North Pendleton Street Middleburg VA
Fully refundableReserve now, pay when you stay
The price is CA $757 per night from Jul 23 to Jul 24
CA $757
CA $937 total
Jul 23 - Jul 24
includes taxes & fees
9.2/10 Wonderful! (403 reviews)
"Staff were very nice and knowledgeable about the history of the resort. My stay was very relaxing. I also enjoyed the zip-line tour. I recommend trying one of the salamander adventure activities."

Reviewed on Jul 3, 2026

Salamander Resort And Spa
The Red Fox Inn & Tavern

The Red Fox Inn & Tavern

4 out of 5
2 E Washington St Middleburg VA
The price is CA $575 per night from Jul 6 to Jul 7
CA $575
CA $656 total
Jul 6 - Jul 7
includes taxes & fees
9.6/10 Exceptional! (441 reviews)
"Amazing staff and service and very comfortable. We'll be back!"

Reviewed on Jul 3, 2026

The Red Fox Inn & Tavern
Hyatt Regency Dulles International Airport

Hyatt Regency Dulles International Airport

4 out of 5
2300 Dulles Corner Blvd Herndon VA
Fully refundableReserve now, pay when you stay
The price is CA $180 per night from Jul 5 to Jul 6
CA $180
CA $207 total
Jul 5 - Jul 6
includes taxes & fees
8.8/10 Excellent! (1,810 reviews)
"Clean room. Nice staff."

Reviewed on Jul 4, 2026

Hyatt Regency Dulles International Airport
See all 1,014 properties in Middleburg
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Stay near popular Middleburg attractions

A waterfall, a river, and a house in the background.

Glenwood Park

10.0/10 (2 reviews)
Explore the great outdoors at Glenwood Park, a lovely green space in Middleburg. Visit the area's spas, or simply enjoy its restaurants.
See properties

What to do in Middleburg

Leesburg Premium Outlets Shopping Tour

Leesburg Premium Outlets Shopping Tour

CA $125
per adult
Leesburg Premium Outlets Shopping Tour
Luxe Day Trip: 3 VA Wineries & Optional Tasting-Inclusive Upgrade

3 VA Wineries Day Trip with Optional Tasting-Inclusive Upgrade

CA $166
per adult
3 VA Wineries Day Trip with Optional Tasting-Inclusive Upgrade
See all activities in Middleburg

Frequently asked questions

How much does a Middleburg vacation package cost?
You'll find cheap prices on Expedia for your Middleburg escape. However, factors like your choice of hotel, the season and length of stay will influence how much your vacation to Middleburg costs.
What are the cheapest months to go to Middleburg?
January, April and September are great times to look for cheap Middleburg vacation packages. Choosing to travel in quieter periods means you can typically find lower prices on accommodations and flights.
How many days is enough for Middleburg?
When planning your Middleburg vacation, a handful of days will be enough to see the best spots. Make sure to check out Chrysalis Vineyards — it's one of the most popular attractions in this destination. If you're after more activities, consider basing yourself here and venturing off on some day tours from Middleburg.
Is it worth booking a vacation package to Middleburg?
It's easy to see why a Middleburg vacation is on the must-do list of many travellers. Well-known attractions like Glenwood Park are just the beginning of things to keep you busy here.
How to find the best Middleburg package deals?
Landing a cheap Middleburg package deal is easy with Expedia. Once you've entered your destination and trip dates under our "Packages" tab, set your maximum budget, add a few filters and see what's available. You can fine-tune your search by "Amenities," "Property type," "Popular locations" and more. Order the results by "Price: low to high" to discover the most economical Middleburg package deals. Want a simple trick to score the biggest savings? Have some flexibility with your departure dates and consider travelling on a weekday, when prices are generally lower.
Is it cheaper to book a Middleburg vacation as a package?
Expedia vacation packages are designed to help you keep more money in your pocket. Bundle your flight, car rental and hotel into one great-value price and enjoy significant savings. You'll typically get a better deal than booking each component separately. And you'll still get the freedom to create a customized Middleburg vacation by choosing your preferred accommodation type, airline and car class.
When to book a vacation package to Middleburg?
If you're planning an impromptu Middleburg vacation, check out our last-minute deals that can be booked up to a week before you take off. Prefer not to wait until the last minute? You can find sensational deals on your flights and hotels by booking well in advance.
How to plan a trip to Middleburg?

  1. Pick the perfect time to travel: Your schedule, favourite season and the type of weather you like can all impact your decision on when to travel to Middleburg.
  2. Set a budget: Factor in costs such as flights, meals and transportation when working out how much to save for your trip to Middleburg. Then, pick a property that matches your budget, whether that's an economical stay or a lavish retreat.
  3. Decide how many days away: Start by compiling a list of the attractions you want to experience in Middleburg. Then, estimate how long you'll need at each, along with any travel time.
  4. Combine your accommodations and airfare: After you've nailed down your trip dates and duration, lock in the perfect Middleburg vacation package for you.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.